


The Trap 2: Dinner and a Show

by BlueEyedArcher



Series: Outlast One-Shots [43]
Category: Outlast (Video Games)
Genre: Alternate Universe - College/University, Anal Fingering, Blackmail, Crossdressing, DInner and a show, Forced Orgasm, Grinding, M/M, Public Masturbation, Rough Kissing, Rutting, Semi-Public Sex, Sugar Daddy!Eddie
Language: English
Status: Completed
Published: 2018-01-14
Updated: 2018-01-14
Packaged: 2019-02-16 12:56:27
Rating: Explicit
Warnings: Rape/Non-Con
Chapters: 1
Words: 3,646
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/13054452
Author URL: https://archiveofourown.org/users/BlueEyedArcher/pseuds/BlueEyedArcher
Summary: Part 2 of a The Trap!Waylon request. A lot of people enjoyed seeing poor college student Waylon crossdressing and falling prey to Eddie. This is the follow up of the first where Eddie blackmails Waylon into have dinner with him and some very sudden spur of the moment sexual interactions right there at the table.





	The Trap 2: Dinner and a Show

**Author's Note:**

> Please let me know what you guys think.
> 
> (Art compliments of @Zeck143 on tumblr. They are amazing and deeply appreciated and wonderful. Thank you Zeck! )
> 
> (Also, this has been updated with art.)

“I’m not some easy fuck!” The blonde male cried out in anger, screaming at the wall in disbelief. He threw the pair of white flats at the wall and watched them plop down in pitiful rage. His eyes brimmed with coming tears as he stared down at the message on his phone. Two days. He had spent two days in the embrace of that lunatic from the community center and now, now he wanted to take the male out for dinner. Of course, not without a bit of blackmail to follow it up. He had a collection of pictures stocked up from all the times he had fucked Waylon into the guest bed. Pictures of his body ravished and marked in such intimate ways, cum pooling out of his poor abused hole, filled from so many rounds in so few days. He didn’t know it were possible for one man to cum so much in so little time. He was an animal. An absolute beast! And Waylon….enjoyed every fucking second of it.

 

That was the worst part of it all. He enjoyed it. Not entirely from the start but by the end of the first round, he was hooked. Crying out the brutish man’s name, grasping and clawing at his shoulders, the bedding, the frame, anything he could get his fingers around as he was screwed mercilessly. And at the end of each round, Eddie had taken a picture of the male, disheveled and broken from pleasure, the signs of cum covering his body, staining the sheets and his soiled panties. His hands were so gentle across his body. So careful and loving. His lips were a soft caress where his hips were punishing in their pace, frantic to expel their love in large foreboding loads.

 

Despite his anger and the hours of cursing and telling himself he wouldn’t go. He wouldn’t do it. He still found himself, waiting by the bus stop at a quarter to eight, wearing yet another set of his ex-girlfriend’s forgotten clothing she left behind after the breakup. White panties, a pair of white knee high stockings with a matching garter and lace on the hems. He managed to find a red skirt that was an inch short of his knees, a white bra and a black tank top. He had a white blouse buttoned up over top of it, the bra having enough padding inside to help make the look work. He fixed his hair up like before with much effort and he wore the same set of flats since they fit and felt okay last time. Matching the stockings. He didn’t do anything with make-up since Eddie had wiped it all off of him last time. His embarrassment continued like before as he held his knees together and folded his hands in front of himself out of modesty, holding his skirt down from the slightest gusts of wind. His phone tucked safely into his bra like before since this outfit failed to have pockets.

 

He didn’t have to wait too long before the familiar beat up old red pick up pulled up to the curb and Eddie leaned across the seat to push the door open for Waylon. He was more dressed up this time in a nice pair of dark slacks, a white button up long sleeve with a black vest over top. He wore a nice formal jacket and tie, making Waylon feel even more out of place. Those hungry blue eyes scanned over his body with a smile as he took in the clothing choice of his date. Seeing Waylon had done as requested and wore a skirt again. Waylon was nervous entering the vehicle, he gave a quick glance around to ensure nobody was watching that knew him before he slid into the seat and shut the door. As he buckled his seat belt, Eddie put the truck into drive and pulled back out onto the road, one hand one the steering wheel and the other moving to rest on the blonde’s knee. “You look beautiful darling. Especially with your hair pinned up like that. You have such gorgeous eyes.”

 

Waylon offered a nervous smile and nodded, reaching a hand up to tuck a straying strand behind his ear. His hands remained resting in his lap, fingers curling into the hem, even as Eddie’s hand threatened to trail up a little higher and explore beneath. Waylon knew Eddie had already seen every last part of him. There was nothing left that he could hide but even now, Waylon held onto those slight shreds of dignity in his mind. Hoping that he could bar the entry from his private area once more. Erecting an imaginary barrier. Eddie seemed to notice or it was just mere coincidence but his hand retreated from the clothed knee and returned to the steering wheel. “Wh-where are we going?” His voice was soft, drifting with his nerves but he managed some form of courage to speak up.

 

“I’ve reserved us a place for dinner. It’s a nice place, I promise. I know the owner so we can have our own private room. Have you heard of the Asylum Lounge?” Waylon gave a short nod of affirmation. He has heard of it. It was a new establishment that opened in the city. Not the kind of place just anyone could get into and it had a very strict dress code. It was a fine dining establishment up top with a killer view of the city and a hardcore club and supposed drug den down on the lower levels. All kinds of shady characters linger there, but that’s just what Waylon has heard from Miles so it can’t all be reliable. Just college town gossip and rumours.

 

The establishment was on a section of prime real estate, resting atop a hill overlooking the city up a privately owned drive. Special invites got them through a set of iron gates with large burly bouncers standing out front. They seemed friendly enough when they spotted Eddie, chatting with him briefly as he passed over a gilded paper, folded neatly with shining letters forming the name of the establishment on the front. It had a black and gold design with a red marking in the lower corner that showed it was from the owner himself. Pulling up, they parked down along the side and Eddie got out of the vehicle first, coming around to hold the door open for Waylon. It was a bit windy so he wrapped an arm around the male and used his body to block the strong cold gusts from uplifting the smaller blonde’s skirts.

 

He guided him around to the front door where he was let in by a separate pair of security, just as big and intimidating. Their cold stares drilling into Waylon as they passed. Entering a well lit hallway,decorated in bright white lighting and silver paneling giving it a futuristic look. There were four sets of elevators on either side of the hallway. Ones that went up to the restaurant and ones that went down to the lower levels where the club was. Both had a special key card needed for access. One Eddie happened to have tucking inside the inner pocket of his vest. He guided Waylon over towards the left side of the hallway where he swiped the card across the keypad. It was recognized immediately, displaying a green light “Welcome” that was both visual and audible with a mechanical female tone. The elevator doors dinged and parted, allowing them to enter.

 

It was a short ride up to the restaurant and when it opened, there was mood lighting and soft jazz playing from the speakers. There were no open seating tables. Everything was a small private circular booth with high walls that prevent others from eavesdropping or staring. There were massive fish tanks built above the overly plump cushioned seating giving more life to each area, filled with exotic fish and pale blue lighting. A well dressed female in a short dark skirt and button up, wearing a mask that reminded Waylon of phantom of the opera or masquerade types, she had her hair done up in a neat bun and spoke in a soft polite tone. Guiding them to the back of the restaurant where large viewing windows and a balcony looked out over the city skyline below. There was an outdoor dance floor and bar for those who wanted to enjoy the evening, dancing to the slow jazz by city light. Their booth was to the right and over two from the windows, only half of it was fish tanks, the other half allowed an uninterrupted view through the large windows. Away from any prying eyes that might be on the balcony.

 

As Waylon slid into the booth, Eddie ordered red wine for the both of them, with waters on the side. Not allowing Waylon to interject at all but it was apparent the larger male wanted them to be alone as quickly as possible. He slid into the booth right up beside Waylon, making it so they were next to the window. Waylon was surprised when they were shifted closer, expecting a cold chill to roll off of it, instead it was just as warm as the rest of the place. A pleasant heat that wasn’t too hot or too cold. A perfect balance in between. Everything was a perfect balance, settling the mood with ease. Between the just right volume and pace of the music, enough to be noticed but not to distract.  “Come closer darling. Let me get a look at you.” Eddie cooed, wrapping an arm around Waylon’s waist and pulling him closer so he was tucked up against his side. Very nearly about to pull him right up into his lap. Eddie pressed a kiss to the smaller male’s temple as the hand around Waylon’s waist caressed his hip, fingers moving towards his thigh and curling up underneath the hem of the skirt, bunching up the material.

 

The action only ceased when the masked waitress returned with their drinks. Eddie gave her a polite smile that was more strained than Waylon has ever seen it before. He watched as the woman placed two glasses of water before them, then poured them each a glass of red wine and set the fluted glasses down. She returned the wine to a bucket of ice that set in the center of the table to chill. An wooden platter with artisan bread was set before them for them to nibble on with their wine while they waited for their meal. The waitress took their order, Eddie once again ordering for Waylon, something that sounded Italian to him before the waitress scurried off to complete the order. Leaving them alone in their own little haven once more, at least to Eddie’s delight.

 

Luckily enough, he was spared from the traveling hands as the larger male offered him a slice of the fresh baked bread, spreading a sweet butter across it for his darling to try. One hand cupping his chin gently as he guided the piece to Waylon’s lips, allowing him to try a bite and leaving him to chew a bit awkwardly. Eddie’s fingers gently trailed down his throat, brushing aside the long blonde locks as he caressed the flesh, leaning in to kiss at his jawline and down to the pulse point, tilting Waylon’s head back in the process.

 

Waylon swallowed thickly, closing his eyes as the larger raven haired male mouthed at his throat in such a way. He was both relieved and a bit frantic that nobody could see them. Should things get out of hand, he was on his own. But should things get out of hand, he didn’t think these were the type of people who would be good natured enough to step in and intervene in another man’s affairs like this. He doubted even if he were to scream rape, not a soul would come to aid him. That only furthered the increasing panic inside him.

 

Luckily enough, the gestures were brief as Eddie straightened back up, returning his hand to wrap around Waylon’s waist as he took his glass with a free hand and sipped at his wine. His deep blue orbs turning ever so slightly to watch Waylon in adoration. Occasionally fixing a fleeing strand of blonde that escaped his hair pins or to brush his fingers over Waylon’s cheek lovingly. When they were nearly out of bread from Waylon’s nervous grazing, Eddie stopped him, leaning down to capture the male’s lips in his, swapping the taste of the wine, it’s bitter complex flavors intertwining with a sweetened aftertaste that lingered on Waylon’s tongue. The exchange was brief but deep, a lingering hunger that found its way inside the smaller male and coiled within his chest with a warm fluttery feeling.

 

He felt saved when the waitress returned to check on their glasses, refilling Waylon’s ice water and placing two platters on the table before them. Both were an elegant plating of fancy pasta, possibly handmade within the hour by the kitchen staff, a red marinara sauce that was rife with elegant spices and rich expensive cheeses melted over top of it. Fresh Parmesan was grated over each and it was garnished with edible green sprigs.

 

 

The rest of the meal was eaten in silence once they were left alone. Eddie had relinquished his hold on Waylon so he could attend to his meal in peace. He was still nervous but his empty belly had him cleaning his plate. It helped that the food was insanely good and probably just as insanely expensive. He dabbed occasionally at his lips to clean off any offending sauce and used the large cloth napkin to protect his lap from escaping pasta or dripping sauce. The meal size wasn’t large, more of a petite display of beauty and elegance but it was fine by Waylon since he mostly filled up on bread and felt as if he could barely finish his dinner.

 

It wasn’t exactly lady like when he was done, wiping his mouth with the napkin, he leaned back against the cushions, giving Eddie a brief sideways glance. Only to find the male had only eaten half of his meal and was intently watching Waylon the entire time. A shiver ran through the smaller male at that reminder, worsening at the hungry smirk the larger male provided upon eye contact. Eddie wasted for the waitress to come clear their plates, dismissing her quickly soon after before patting his lap. Beckoning Waylon to take a seat in it. Waylon was confused at first but Eddie was patient, wrapping an arm around the smaller male’s waist and pulling him around to sit, straddling his hips, the skirt started to ride up.

 

Behind Eddie was the massive glass windows allowing Waylon to see over his shoulders out at the city lights. It would have been breathtaking were he not currently feeling the rather large and far too familiar bulge pressing up between his legs. With only the thin silken fabric of the panties providing a barrier between, he felt the large hands caress his clothed rear. The privacy of the booth helped make it so nobody else would happen upon their little scene as Eddie’s palms rubbed against the underneath of the skirt and spread the panties outwards away from Waylon’s skin before letting go. The elastic lining causing them to snap against his skin and draw a barely stifled yelp from his lips. He gripped Eddie’s shoulders, pressing his reddening face into the thick dark material of his coat. “How about a little after dinner entertainment darling?” He purred into Waylon’s ear. “Careful, if you’re too loud, the whole restaurant will hear you.” He punctuated his warning with a nice firm grope of Waylon’s cheeks and a roll of his hips, grinding up into Waylon’s smaller bulge. The fabric rubbing against his sensitive member. He bit his lip as the motions continued.

 

“Don’t worry darling, i’m not going to put it inside. But your poor little panties won’t be lasting much longer.” He’s hands shifted to hold onto Waylon’s hips as he ground up against the smaller blonde male. Waylon bit his bottom lip harder but it was only a brief attempt before Eddie captured his lips into a deep kiss. The taste of wine overthrowing all other flavors and coating Waylon’s tongue. He felt the glowing warmth of Eddie’s cheeks against his own before the larger male broke their connection to catch his breath. Releasing a slow exhale and pressing their foreheads together. “I want you to grind your hips against mine darling. Don’t worry, nobody can see us.” He reassured before giving Waylon’s rear a nice firm slap, skin meeting skin with a sharp crack that had Waylon swallowing down the cry that threatened to rise.

 

He closed his eyes and started to work his hips down, rubbing against Eddie’s. Rolling them and using Eddie's shoulders to balance out. His features heated up, breathing became more frantic and breathier, more gasping and deep desperate sighs. His little bulge became something much more that stretched out the cute little pair of panties. Eddie’s fingers found their way to the edge ad would pry at the material to add more conflicting friction and pressure to Waylon’s movements. At one point he felt Waylon’s mind was becoming more distracted, noticing how his hips would cease or he’d hold in place for a moment or two as if catching a break or more precisely, trying to hold back.

 

Eddie moved his hands, one rising to Waylon’s lower back, caressing the delicate dip of his slender frame with his other hand slid lower, fingers slipping between the soft white fabric, feeling the wetness that had formed from precum. He swiped his fingertips over it a few times to gather enough dampness on his digits before sliding back along his taint to the dip between his cheeks. Waylon’s body tensed as his well used hole was spread apart by the two intruding digits. Sliding inside with relative ease, had Eddie not been the one behind the twitching quivering mess that was his darling’s entrance, he would assume the smaller blonde was an easy lay about town.

 

Without hesitation, his fingers began a steady easy thrust rising and falling inside of Waylon, seeking out the desired spot. Waylon gasped, thighs tightening around Eddie’s hips as they rolled forward wantingly. He pressed his head into the crook of the larger male’s neck and gasped, barely stifling the moans falling from trembling lips. His fingers curled into the thick expensive fabric of his coat, grasping desperately at his lapels as he ground down harder and more desperately. The cushions of the booth started a slight creaking from the movement. The sound of weight slipping and sliding against the fabric holding back the explosion of stuffing. It wasn’t loud enough to be overheard by anyone nearby but it was getting there with Waylon’s gasping breathes and muffled sounds of pleasure. His thrusting fingers drove deeper, hit harder to urge Waylon forward. Pushing more firmly against that special little bump inside as he was pressed to the very edge. He held it there, rubbing and massaging that place until he was certain they both were dangerously close to losing it.

 

He pressed their lips together, capturing Waylon’s in a starved attempt to swallow the male up, to devour his heart and soul, pressing him back and pulling him forward at the same time. Neither caring that the table was forced into Waylon’s back as hips ground up and forward. The simultaneous push of eager fingers forcing both men into a shuddering climax of teeth and tongue and devoured sounds between the two of them. Eddie’s boxers experienced the spilling warmth inside but it was a pleasant sort of sticky heat that he enjoyed. Waylon on the other hand felt pleasure reminiscent of the experience he was put through over the last couple days followed up by immense shame as his own seed started to leak out of the fragile panties. The white dinner cloth remained a barrier between Eddie’s black slacks and Waylon’s white panties, catching a good amount of the spilled seed. He used the other cloth to wipe Waylon’s thighs clean as well as his own hands.

 

Eddie was deeply satisfied with the turn of events that evening and slid Waylon off of his lap. Setting the deeply embarrassed and mortified blonde aside while he removed his jacket to drape around Waylon’s shoulders. It was big enough to swallow him up and provide some comfort and the illusion of privacy and protection from anyone nearby who may be watching. Eddie smiled, drawing Waylon up on shaky legs and resuming his arm wrapped around the male’s waist, parading him throughout the establishment as the smaller male performed a walk of shame. Feeling as if all eyes were somehow following him about. As if their dirty deed was known and acknowledged by all within the restaurant.

 

Eddie paid at the front desk where they had entered, providing a little extra incentive to the waitress due to the mess they made before swiping his card at the elevator so they could return to the truck. Waylon’s embarrassment had him red faced and head turned down the entire time. The ride home was long and before they even got halfway back to Waylon’s side of town, the blonde had fallen asleep in the truck. Wrapped up in Eddie’s coat still with the heaters cranked up to provide additional warmth and comfort. It was all the reason Eddie needed to take the next turn towards his own home. Intending to spend even more time with his adorable little minx.

 

 

 

 

 

 

 

 


End file.
